When you’re a small market team like the Milwaukee Bucks, you’ve got to make your free agent signings count. Unlike teams in New York, Los Angeles, or Miami, the Bucks simply can’t afford to miss in free agency. They’re not a top-of-the-list destination for many free agents – at least until recently – so they haven’t had the luxury of knowing they’ll get another chance at the best free agents on the market next summer. When they take a swing at someone it’s imperative that the signing pans out.
But no organization gets every free agent move right. The NBA is littered with stories of player signings that, in retrospect, would have many of us scratching our heads and wondering how in the world a GM could have gotten his team’s owner to sign off on such an absurd deal. The Milwaukee Bucks are no exception.
Thankfully, the current regime has done a great job of finding free agents to help retool the roster. The presence of established stars and the regular threat of title contention has made John Horst’s job easier but give credit where credit is due – Horst has done a heck of a job since taking over in 2017.
Consequently, many of the names on this list might seem like a blast from the past. Let’s take a trip down memory lane and look back at some of the worst signings in Milwaukee Bucks’ history.
5. Tim Thomas got the bag but never got better in Milwaukee
After an impressive freshmen season at Villanova, Tim Thomas was drafted 7th overall by the New Jersey Nets and then quickly traded to the Philadelphia 76ers. He had an impressive rookie year averaging 11 points and 4 rebounds per game while shooting a solid 36 percent from behind the arc. His athleticism and versatility caught the eye of the Bucks and in 1999 he was traded to Milwaukee.
Thomas played some of the best basketball of his career with the Bucks. He was so impressive that then-owner Herb Kohl deemed him a “vital part of the team” and was determined to re-sign him.
Thomas ultimately signed a 6-year, $66 million dollar deal that was representative of the star potential that the Bucks clearly thought he had. Unfortunately, Thomas never quite reached the ceiling that the organization thought he had.
Thomas wasn’t a slouch by any stretch. He’d continue to average about 12 points and 4 rebounds per game during his time in Milwaukee which is solid. But not for $11 million a year. Remember, this was back in the early 2000s. Today $11 million a year for 12 points and 4 rebounds a night isn’t bad. It’s not good, but it’s not enough to land you on the “worst signings in team history” list. Back then it was inexcusable.
Tim Thomas’s time was uneventful and full of unfulfilled potential. For a player that Ray Allen once said could be the best in the league, you’d have hoped to see a lot more.
4. Mirza Teletovic
It’s easy to see why the Milwaukee Bucks would have thought that signing Mirza Teletovic would have been a good idea. Coming off a season where they were one of the worst three-point shooting teams in the league, the Bucks were desperate for shooters. Mirza had just had a career year for the Phoenix Suns. It seemed like a perfect match.
After coming off the bench to average 12 points a game on 39 percent shooting from behind the arc, the Bucks inked Teletovic to a 3-year, $31.5 million dollar deal. At the time it seemed like a bit of an overpay but was the pre-Giannis Bucks, they weren’t exactly a city free agents were begging their agents to get them to get to. And Milwaukee really did need three-point shooting.
Maybe he was misused by Jason Kidd or maybe he simply duped the Bucks into believing that his career year in Phoenix was his new floor but Mirza never panned out the way that the Bucks were hoping he would. He never averaged more than 7 points a game in Milwaukee and was gone after two seasons.
At the time this was the kind of signing the Bucks had to make. They needed the shooting Mirza offered and there simply weren’t better options available. But looking back on it it’s certainly one of the more disappointing signings in recent memory.
3. Bobby Simmons
In a story that is beginning to sound familiar, the Milwaukee Bucks signed Bobby Simmons after he had a career year and then quickly fell into buyer’s remorse. After a few quiet years in Washington and with the Clippers, Simmons finally broke out during the 2004-05 season, starting 74 games for the Clippers, averaging 16 points per game on 44 percent shooting from deep. He won the NBA’s Most Improved Player award the year before hitting free agency.
That summer, the Bucks signed Simmons to a 5-year, $47 million dollar deal in the hopes that they could get a budding star for under $10 million a year. If it had played out that way it would have been a steal. But, sadly, Simmons could never recapture the spark he had in Los Angeles. Maybe it was the change in climate that did it or maybe he just wasn’t that good to begin with.
His first season in Milwaukee was decent albeit unimpressive. He averaged 13 points per game and shot 42 percent from deep, but that didn’t translate to much success for Milwaukee. They’d ultimately make the playoffs before losing in the first round to the powerhouse Detroit Pistons.
After one mildly successful season, things went really bad for Simmons. He’d miss the entirety of the 2006-07 season with an ankle injury and was never the same player after he returned. He played just one more underwhelming season with Milwaukee before being traded to New Jersey with fellow disappointment Yi Jianlian.
2. Miles Plumlee
The second most successful of the Plumlee trio (sorry Marshall), Miles Plumlee was acquired by the Bucks via trade in 2015. After arriving in Milwaukee he came off the bench in 19 games and averaged a pedestrian 3 points and 2 rebounds per game. What followed was a level of front-office incompetence that is truly mind-blowing.
I don’t know if Plumlee had some dirt on John Hammond or if Hammond owed the Plumlee some favors but somehow, after playing in just 19 games and doing hardly anything of note, Hammond and the Bucks signed Plumlee to 4-year, $50 million dollar contract.
$12.5 million a year! For Miles Plumlee! That’s highway robbery! Maybe the Bucks thought that the contract would look better after Plumlee grew into a player resembling Brook Lopez but the thing is, he never did.
The season after he signed his extension he’d start in 14 games, averaged 5 points and 4 rebounds per game, and didn’t provide anything resembling game-changing rim protection. He was a 6’11 big man who could pull down boards and set screens but for $152k a game, you’d expect a heck of a lot more than that.
It didn’t take long for the Bucks to realize they made a mistake. Plumlee was traded to Charlotte in 2016 and was out of the league by 2019.
1. Larry Sanders
Depending on how you want to look at it, the Larry Sanders signing may or may not make your own “worst signings in Bucks history” list. There was a lot that went into his fall from grace with the Bucks. But there’s no doubt that his time in Milwaukee didn’t come close to touching the potential that Bucks fans had for him.
After being drafted out of VCU in 2010, Sanders had two fairly quiet seasons with Milwaukee before breaking out. During the 2012-13 season, he put himself out there as a name to watch with his relentless energy, great rim protection, and passion for the game. This was a guy who would smack opponents’ shots into the 5th row then clap in his face and talk smack immediately after. He brought fire to the game, and fans loved him for it.
Sanders had all the tools to dominate the defensive end of the floor. The Bucks and their fans deservedly thought that they had found someone special. He seemed like he could be the lynchpin of what could eventually be a suffocating defense. To help bring that to life, the Bucks signed Sanders to a 4-year, $44 million dollar deal ahead of the 2013 season.
It wasn’t long into the 2013 season that things started to come apart for Sanders. He was sidelined for 25 games for his role in a nightclub fight and tore a ligament in his thumb in that same fight.
He would return in 2014 but not for long. In March of that same season, he broke the orbital bone near his right eye after taking an elbow to the face from James Harden. That injury would sideline him for the rest of the season.
Two drug-related suspensions would follow, after the second one the Bucks announced that they were buying out the remainder of Sanders’ contract.
Sanders would eventually check himself into a rehabilitation facility, question if basketball was truly his calling, and pursue his artistic passions, all before returning to the league in 2017, this time for the Cleveland Cavaliers.
Of all the signings, Sanders is the one that bugs me the most. He had so much talent and passion and you could see that in the way he played. But he also had some real off-the-court issues he needed to sort out. It’ll be hard to find a Bucks fan who resents Sanders for how things shook out in Milwaukee, everyone wanted him to succeed. But for one reason or another, it never did.